Acetyl trifluoroacetate → 2-Azatricyclo[3.3.1.13,7]decane-5-carboxamide

HRID 623984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623984
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([N:7]3C(OC(C)(C)C)=O)[CH2:5]1)[CH2:11]2)(=[O:3])[NH2:2].C(OC(=O)C(F)(F)F)(=O)C>C(Cl)Cl>[CH:6]12[CH2:5][C:4]3([C:1]([NH2:2])=[O:3])[CH2:11][CH:10]([CH2:9][CH:8]([CH2:13]3)[NH:7]1)[CH2:12]2

Komponenten

4

Edukt 2

HCID 12752924Acetyl trifluoroacetateHCID 89715036Tert-butyl 5-carbamoyl-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate

Produkt 1

HCID 897152042-Azatricyclo[3.3.1.13,7]decane-5-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 100 mL RB flask fitted with magnetic stirrer was charged tert-butyl 5-carbamoyl-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-11 (0.1 g, 0.0357 mmol) in DCM (5 mL). The reaction mixture was cooled to 0° C. and trifluoroacetic acetic anhydride (0.21 g, 0.17 mmol) was added and stirred for 4 hours. After completion of the reaction (reaction was monitored by LCMS) reaction mixture was concentrated followed by trituration with mixture of hexane:ether (1:1) to give Intermediate-12 (0.09 g, yield=90%).

Aufarbeitung

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction was monitored by LCMS) reaction mixture
  3. concentrationwas concentrated
  4. additionfollowed by trituration with mixture of hexane:ether (1:1)
  5. customto give Intermediate-12 (0.09 g, yield=90%)

Quellen und Nachweise

ORD-Eintrag
ord-8335c254284d4d54b47d7308448371f4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303016B2

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